Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediated by Methyltrioxorhenium

Molecules

Maria E. Amato²  Francesco P. Ballistreri²  Andrea Pappalardo²  Gaetano A. Tomaselli²  Rosa M. Toscano¹ 

[1] Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 6, Catania 95125, Italy;

关键词: natural compounds oxidation;    hydrogen peroxide;    methyltrioxorhenium;   

DOI  :  10.3390/molecules181113754

来源: mdpi

【 摘 要 】

We have investigated the oxidative behaviour of natural compounds such as methyl abietate (1), farnesyl acetate (2), α-ionone (3), β-ionone (4), methyl linolelaidate (5), methyl linolenate (6) and bergamottin (7) with the oxidant system methyltrioxo-rhenium/H₂O₂/pyridine. The reactions, performed in CH₂Cl₂/H₂O at 25 °C, have shown good regio- and stereoselectivity. The oxidation products were isolated by HPLC or silica gel chromatography and characterized by MS(EI), ¹H-, ¹³C-NMR, APT, gCOSY, HSQC, TOCSY and NOESY measurements. The selectivity seems to be controlled by the nucleophilicity of double bonds and by stereoelectronic and steric effects.

【 授权许可】

CC BY   
© 2013 by the authors; licensee MDPI, Basel, Switzerland.